반응 #46205

반응 방정식

(3,4-dihydroxy-phenyl)-acetonitrile

2,2-dimethoxy-propane

TsOH

→

2-(2,2-dimethylbenzo[d][1,3]dioxol-5-yl)acetonitrile

수율 20.0%

용매

toluene

반응 조건

후처리

1. 1
   온도The mixture was heated
2. 2
   온도at reflux overnight
3. 3
   기타The reaction mixture was evaporated
4. 4
   기타to remove the solvent
5. 5
   workup.DISSOLUTIONthe residue was dissolved in ethyl acetate
6. 6
   세척The organic layer was washed with NaHCO3 solution, H2O, brine
7. 7
   건조dried over Na2SO4
8. 8
   기타The solvent was evaporated under reduced pressure
9. 9
   기타to give a residue, which
10. 10
    기타was purified by column chromatography on silica gel (Petroleum Ether/EtOAc 10:1)

실험 절차

To a solution of (3,4-dihydroxy-phenyl)-acetonitrile (0.2 g, 1.3 mmol) in toluene (4 mL) was added 2,2-dimethoxy-propane (0.28 g, 2.6 mmol) and TsOH (0.010 g, 0.065 mmol). The mixture was heated at reflux overnight. The reaction mixture was evaporated to remove the solvent and the residue was dissolved in ethyl acetate. The organic layer was washed with NaHCO3 solution, H2O, brine, and dried over Na2SO4. The solvent was evaporated under reduced pressure to give a residue, which was purified by column chromatography on silica gel (Petroleum Ether/EtOAc 10:1) to give 2-(2,2-dimethylbenzo[d][1,3]dioxol-5-yl)acetonitrile (40 mg, 20%). 1H NMR (CDCl3, 400 MHz) δ 6.68-6.71 (m, 3H), 3.64 (s, 2H), 1.67 (s, 6H).

출처